


The Perfect Fit

by blushingsamgirl



Category: Supernatural
Genre: Alternate Universe, Alternate Universe - Fashion & Models, Alternate Universe - Modern Setting, Angst and Fluff and Smut, Angst with a Happy Ending, BFFs, Charlie Being Charlie, Coffee Shops, Drinking to Cope, Eventual Smut, Ex-Girlfriend, F/M, Fashion & Couture, Friendship/Love, Jessica Moore Lives, Model Dean, Model Sam, Model Sam Winchester, Originally Posted on Tumblr, Photo Shoots, Reader-Insert, Reader-Interactive, Sam Winchester-centric, Sam-Centric, Self-Esteem Issues
Language: English
Status: In-Progress
Published: 2016-07-04
Updated: 2017-01-08
Packaged: 2018-07-20 00:38:26
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 7
Words: 17,129
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7383991
Author URL: https://archiveofourown.org/users/blushingsamgirl/pseuds/blushingsamgirl
Summary: <blockquote class="userstuff">
              <p>You’ve always dreamt of becoming the next big fashion designer. Everything changes completely when your best friend/fashion blogger, Charlie, gets an invite to a prestigious fashion show where you recognize an all too familiar face on the runway.</p>
            </blockquote>





	1. Walk, Walk Fashion Baby

**Author's Note:**

> This was supposed to be a one shot for @teamfreewill-imagine and @latinenglishfandomblog ‘s Sam’s Sixty June Jobs challenge on Tumblr but the story grew into something more. Might be a 3-parter or longer depending on how much fun I’m having writing it. Feedback is always appreciated.

You never once thought about fashion as a career. It was just something you grew up with. Having clothing modified from thrift stores and Goodwill just made room in the budget to pay for rent and hot meals. That was the life you knew. In its own way, fashion was a way of normal life for you. Clothing was never something you picked up from a store and wore outright. You’d get used clothing but then you’d apply your creativity and style to make it your own.

Pursuing a career in the fashion industry was an odd choice for you. You were aware of how conflicting it was. Practically everyone in the industry wants to be in the spotlight and there is a lot of superficialities related to it. But it was something you enjoyed and you knew that staying behind the scenes was your forte. So why still stick with the fashion industry? As someone once told you, “Sometimes you have to stop thinking so much and go where your heart takes you. You might regret it if you don’t.” You often wondered what happened to that cute guy who gave you such bold advice.

That was how you ended up here, pins in your mouth dealing with a sprightly, redheaded girl who for the love of everything good and holy would not stop squirming. It was beginning to drive you crazy.

You attempted to speak out the side of your mouth, “Charlie stop moving.” But it ended up sounding like mumbled nonsense.

“Sorry,” Charlie chirped out recognizing your plea for her to stop, “I’m just super anxious, you know?”

You took the pins out of your mouth and gave your friend an honest smile, “I know, Charlie. It’s going to be fine. Just trust me.”

Charlie was your ‘sista from anotha mista’, your best and most fashionable friend. The two of you were assigned as roommates at college but became fast friends once you discovered your mutual interest in fashion. It was a team effort really - Charlie kept you up to date with knowing who’s who in the industry and the latest trends online, while you used your trusty sewing know how to create the latest styles on a student budget. Charlie graduated with a degree in digital marketing and you had a degree in fashion. There was nothing the two of you couldn’t do… if only you could find a couple jobs in your field.

This week, the door of opportunity presented itself with Charlie getting approval to attend a fashion show to represent her fashion blog, _It’s Good to Be Queen_. It was definitely an impressive blog that showcased her know how of the industry and thanks to your sewing expertise, she was able to post unique creations inspired by the latest trends.

The most important decision in attending a fashion show was what to wear. All week long you were figuring out a Y/N original design for her to wear, which typically meant getting something from Goodwill and revising it with your sewing machine. However, Charlie kept changing her mind. She already had three outfits to choose from and was slowly becoming part diva, part anxious nerd. It was starting to become infuriating, so you decided to put your all into this fourth and final outfit.

You switched off her iPod that she insisted on playing “Walking on Sunshine” on repeat.

"But montage,” she trailed off sadly as you gave her a look of annoyance, “come on, _walking on sunshine_?”

“No, Charlie, we’re done. No more _walk, walk fashion baby_. You look fantastic,” you turned her around to face the full-length mirror in your shared apartment.

She gasped in awe as she looked at your creation. It was originally a plain dress that someone’s grandmother wore to church, two sizes too big for her and with a full-length skirt. The floral print of the fabric was gorgeous but the cut didn’t suit her at all. You cut a plunging neckline into it, tailoring it to her curves. With the skirt, you altered it by gathering and shortening it so it would pouf out. It was sexy and cute, like if Tinkerbell met Dolce and Gabbana.

“You’ve done it again my friend,” she smiled briefly before plastering a wider grin on her face that seemed overbearing.

“What? What’s this face? Charlie…” You knew she was about to drop something on you and you began to feel uneasy.

“I kinda forgot to tell you that you’re coming with me tomorrow night. You’ll be my plus one at the fashion show.”

Your jaw dropped in shock, feeling equal parts shock and thrill at the news. But panic set in suddenly.

“I need something to wear!”

* * *

It was the day of the fashion show - showcasing a new menswear collection. It would be your very first professional industry event. You decided on the tried and true LBD but for this event, it meant your little black leather mini. It was the rare item you discovered that didn’t need any alterations to it, it fit you like a glove but never found an occasion to wear it. The black helped it blend into the crowd because fashion folks love wearing the colour, but the leather gave you a bit of an edge.

Even though it was your first fashion show, you and Charlie looked like you belonged there. Or at least you thought so as you arrived at the venue with credentials in hand looking like professionals.

Once you entered the venue, you were mesmerized by how dark the room was, save for the long lit up runway with rows of seating crowded alongside it. You glanced at Charlie who was equally captivated. In an effort to keep professional and not completely fangirl, you delicately reached for her hand and squeezed it. Charlie glanced back at you and nodding her head in acknowledgment and squeezed back in excitement. It was so good to have a friend by your side at this moment

After everyone settled in their seats, a hush fell over the crowd once the lighting changed indicating the show was about to begin. A happy pop-y song began playing and the first model came out. Everyone’s eyes were fixated on the handsome man who wore a perfectly tailored long jacket. He slowly removed it before pivoting at the end of the runway to reveal a classic two piece suit.

Once the next model came out you briefly imagined what it would feel like to have a show like this for your own designs. An entire show with everyone excited to see what your creative mind could concoct and how it would influence what people wore, how it could influence how it made people feel. It was nice to dream in that moment as you stared at the runway.

Your thoughts were interrupted once you looked at the latest model on the runway. He was taller than the others. His hair was long and sleek, bouncing slightly as he walked down the runway in a classic Castiel trench coat in black with a navy suit underneath. He looked debonair and sophisticated, but there was something else about him that made him seem so familiar to you. When he reached the end of the runway he flashed a tiny, closed mouth smile that revealed a dimple on his cheek.

You recognized that dimple anywhere - it was him! The cute guy who gave you the advice to follow your heart’s desire to get into fashion when your major was still undeclared during your first semester of freshman year. The same guy who invited you to his place after that dreadful house party before winter break. It was him. The guy who you used his expert fingers on you as you gave him a handjob because there were no condoms around. There’s no pretty way to cover that fact up. But he disappeared after that night. You wondered what happened to him but now you knew.

Sam was a model and he looked amazing.

You found it difficult to concentrate after that and you tried so hard to not drag Charlie away to gossip about your discovery. That wouldn’t be professional at all. No, you had to sit and force yourself to pay attention - this is your career, Y/N. Just focus.

Thankfully the rest of the show went by quickly, even with Sam showing up on the runway again, wearing a sweater vest ensemble that made you bite your lip and squeeze your thighs together. Perhaps wearing a leather dress wasn’t the best thing to wear, it just made you feel more hot and bothered.

As part of the show finale the designer, Castiel Novak, walked out on the runway with his models beside him. Everyone applauded but Charlie kept clapping madly. She was a fan of Castiel since he brought trench coats back in style in the mid-2000s.

* * *

There was a reception taking place after the fashion show. Charlie went on and on, trying her best to be casual and incognito as you walked past many familiar head honchos in the industry. She’d leaned into you and in an excited hush would announce who we’d pass by.

“There’s Crowley, the magazine editor… Rowena, PR fashion queen… holy shit Y/N, Abaddon is here.”

You couldn’t be bothered at the moment, your mind still busy with thoughts about Sam. You needed a drink to wrap your head around the fact that you just saw him and he was a hot runway model. Free drinks and appetizers were plentiful as waiters walked around with full trays. You picked up two glasses and when Charlie reached to you for a glass, she was taken aback when you chugged back one glass and didn’t let go of the other.

“Whoa, what’s up with you Y/N? I know they’re free but control yourself.”

“Charlie, I recognize one of the models.”

“Huh?”

Suddenly you see him approaching the bar a few feet away from you. You chugged the rest of the other glass in your hand.

“Shit, he’s right there. Don’t look,” you instructed her.

“Who,” Charlie turns to look at the bar, “oh, upcoming model Sam Winchester?”

You pulled her away from looking at him. “No, you don’t understand it’s Sam. The cute guy from that night I decided that I was going to go into fashion. The one who disappeared after we had a connection. The one I praise about all the time. That Sam.”

Charlie had a deer in headlights look, before realization took over, “Wait, Sam Winchester is your Sam?” A huge grin appeared on her face, “This is fate Y/N! Can’t you see? He’s here, you’re here. You both look fantastic.”

“I’m not a model, Charlie! I look ridiculous - why did I think black leather was ok. Ugh, why is this happening to me right now?” You whined, regretting not spending more time choosing an impressive outfit.

Charlie was determined to support you, “No, you need to march over there and say ‘ _hello sexy man, remember me, I’m the sexy woman you knew from college. We’re both sex… uh, and into fashion… boo-yah’_.”

“Boo-yah?” You asked incredulously.

“I don’t know, your freakout is making me nervous - and come on, Abaddon is here. _The_ Abaddon. I need to fangirl with you.”

“Y/N, that you?” a deep voice interrupted your bickering.

The two of you turned to see Sam, holding onto a bottle of water in one hand and looking even more graceful if that were even possible.

“Wow! Hi! It’s been a long time,” you smiled, feeling super awkward and knowing what to say.

“Yeah, a really long time,” Sam replied with his gaze fixed on you, briefly giving you the once over.

In that moment you wished for something crazy to happen - a random bolt of lightning in the sky to strike you down, for some crazy kidnapper to take you away - anything to get you out of this awkward situation.

Charlie could tell you needed some help and introduced herself before proceeding to talk about Castiel’s designs and how big of a fan she is. Thank god for Charlie, your very blessed best friend.

Another waiter passed by with a tray of drinks and Charlie finally got a glass of the signature drink, while you picked up your third. Third - ok, that’s good, you’re sober enough to count your drinks. No more after this one, though.

“Hey Cas, I want you to meet some friends of mine,” Sam called over Castiel to meet you and Charlie.

It was the first time meeting a real fashion designer. Your nerves were shot, so you took a sip of your glass that was still half full.

Castiel approached the three of you, dressed in his classic tan trench coat, wearing a black button-up shirt underneath. Only he could pull off a look like that and make it super chic.

“It’s an honour, Mr. Novak,” you nodded.

Charlie’s eyes glazed over in wonderment, her jaw slacks as she fawned, “Whoa, it’s really you.”

Castiel looked at you and Charlie with a twinkle in his eye and a slight smile on the side of his lips. It was obvious that he was pleased with the reaction his presence brought out.

“Call me Cas,” he charmed with a gruff voice, shaking your hand first then Charlie’s.

The excitement of the moment took away your nervousness of the situation. Soon, the four of you began chatting about fashion shows and Castiel’s new collection.

You were at ease until he questioned Charlie about her outfit.

“I’m sorry to interrupt, but this?,” he gestured to Charlie’s dress, “What is this?”

Crap, he hated it. _What is this?_ That’s never good phrasing of a question.

“It’s a Y/N original,” she announced confidently gesturing to you. You blushed, flattered of your best friend’s high regard for you in front of an actual fashion designer, but also embarrassed if Castiel Novak thought you had no right to be in the fashion industry. You hated being in the limelight even just slightly.

“I’m in love with it,” Cas stated plainly looking at you, “you’ve got talent.”

You stood in shock thinking you lost your sense of hearing. Did he say he loved it? Was this real - a confirmation of your talent by a real fashion designer?

“Actually, Cas, I have more questions if you don’t mind,” Charlie hooks her arm with Cas, dragging him away leaving you and Sam alone. Wiggling her eyebrows at you before turning away.

“Wow,” Sam added with a smile, “you did it, fashion designer.”

You looked at Sam, “Well, just a fashion degree, trying to be a seamstress for now.” You clear your throat, “But you’ve made an impression on the industry. Runway model, huh?”

“Yeah,” Sam chuckled, “Uh, first runway show actually. One gig led to another and another. I don’t think law school was meant to be,” he said sadly, “But you look great.”

You hated hearing the sadness in his voice and decided to jest with him. “Thanks. You look meh,” you joked, giving him the so-so hand gesture.

The both of you laugh, finally feeling more like yourself.

“There’s the Y/N humor I remember. God, it’s so good to see you. You know I-”

“Sammy!” called out a voice across the room.

“Ugh, that’s my brother. I gotta go, but I really want to stay in touch.”

“Give me your phone,” you insisted. When he handed it over you texted yourself and handed it back to him, “there now you’ve got my number, I’ve got yours and you can no longer disappear from my life again.”

“About that-”

“No, I don’t wanna hear about it. Text me later, I’ll be expecting it.” You teased.

Sam took your hand, squeezing it, “It was really good seeing you.”

“You too, Sam.”

Sam walked away and for a brief second, you wondered if you would hear from him again.

You stood there, still processing what happened when a waiter walks by with a tray of drinks. After grabbing another glass of liquid courage, you made your way into the crowd, hoping that you would be able to network or schmooze with at least one interesting person at this event.

* * *

“Come on, Y/N, up we go,” Charlie instructed.

“Huh?” You stirred awake, at the feeling of your arm being pulled.

“I just paid the fare. Let’s say night-night to Mr. Cab driver.”

Your eyes widened, how did you end up in the back of a cab? The last thing you remember was getting another glass of whatever drink they had on the platters. You attempted to get out of the cab as quickly as you could, with Charlie helping you out.

Once you arrived at your apartment, all you wanted to do was slump into your bed and Charlie being your bestest friend, dragged you to your room to do just that.

“How many glasses did you have tonight, Y/N? I don’t think I have ever seen you this drunk before,” Charlie stood dumbfounded by the foot of your bed.

“Fee drinks Char. When Rome, do Rome,” you driveled.

“I guess,” Charlie chuckled at you before sighing, “well I’m off to bed, you better sleep this off since we are gonna need to talk about everything in the morning.”

“Every wha?” you asked confused

“Peace out, bitch!” She called out as she left your room.

You were exhausted, still a little drunk, and wanted nothing more but to get out of the leather dress that encapsulated you. Stretching out your arms seemingly unable to grasp at the zipper and you knew your body wasn’t cooperating

“Char!” You grumbled, feeling helpless.

You were clumsy and illogical in your drunken state. Moving around the bed, you felt a lump and noticed your clutch purse. The alcohol in your brain told you that you needed to call for help, so you removed your phone and proceeded to call Charlie.

“Hey, didn’t expect you to call me,” a sleepy soothing voice greeted you.

“Help!” You pleaded frustratedly.

“What’s wrong?” the voice asked concerned.

“Need outta my dress. S’too tight.”

The voice chuckled out, “are you drunk?”

“Aww yeah,” you replied with a smile.

The laugh grew louder and that’s when your brain finally caught up with the fact that you had drunkenly called Sam instead of Charlie.

“Ohmygod, Sam s’that you?” You happily questioned.

“Yeah, Y/N, it’s me,” Sam confirmed with a smile.

“S’good to see you tonight. Scary… but good.”

“Scary? Why?”

“Cause s’you look s’good, big model man ‘n a fancy suit n’ sweater vess. M’dress not fancy enough f’that.”

“I thought you looked great in that dress tonight,” he replied somehow deciphering your drunk babbling, “black leather… yeah, really great.” he breathed out as if picturing you in front of him.

“I didn’t even make this dress,” you sulked, “I want it off. Help me get off Sam.”

Sam chuckled again, making your heart flutter at the sound and still unaware of your choice of words. You didn’t care if he was laughing at you or that he wasn’t helping you out of your dress like you asked him too. Hearing him happy lifted your spirits and you giggled along with him.

“Oh, I’d love to help you out in all sorts of ways if I was there,” he sighed audibly, a tinge of want noticeable in his voice.

“Can’t believe you’re a model, Sam… mmmm, I missed you.”

“Missed you too. You know, when I saw you tonight…” Sam trailed off as you involuntarily yawned.

“What Sam? M’still listening.”

There was a pause.

Panicked at the silence, you called out, “Sam?”

Sam spoke softly and you could tell he was still smiling, “I’m still here. Let’s talk tomorrow, ok? Get some sleep.”

“Mmkay, Sam. Night night,” you said as you cuddled into your pillow, forgetting to end the call.

Sam kept listening when he realized you didn’t touch your phone. He smiled to himself when he heard the sounds of your relaxed breathing as you fell asleep.


	2. The No Good Day

**Summary for the Chapter:**

> It’s the day after the fashion show and you don’t remember a thing. You get an invite from Sam to go out for coffee but everything goes wrong.

**Notes for the Chapter:**

> Text exchanges are bolded and italicized. I’ve been listening to nonstop 1980′s pop music while writing this series.

* * *

The loud peppy sounds of a familiar pop [song](http://t.umblr.com/redirect?z=https%3A%2F%2Fplay.spotify.com%2Ftrack%2F05wIrZSwuaVWhcv5FfqeH0&t=MWVhMTdkZGNkYjVkYjJlM2UzMTlkMGFmY2JmYWEzNTg0MmZkMTA3YixDa3Q4MzhSTQ%3D%3D) stirred you from your peaceful slumber.

_I used to think maybe you loved me, now, baby, I’m sure  
And I just can’t wait till the day when you knock on my door_

Your eyes opened wide. No, it couldn’t be.

_Now every time I go for the mailbox, gotta hold myself down  
Cause I just can’t wait till you write me you’re coming around_

Oh God no, not this again.

You try to get up, finding it hard to move. Oh, right, you were still wearing your leather dress - not exactly the stretchiest of fabrics.

Managing to get your ass out of bed, you dragged yourself to open your bedroom door. The other side of the door revealed your way too peppy roommate singing and bouncing around in the living room.

“I’m walking on sunshine, WHOA!”

“Come on,” you complained.

“I’M WALKING ON SUNSHINE, WHOA!”

“Charlie-”

“Nope, no it’s not time for talking, we are _walking on sunshine, don’t it feel good_ ,” She recited as she takes your hand, dragging you to your small living room, prancing around your zombie-like state.

“Ungg, it’s too early,” you complain, slumping down on the couch as she continued to shimmy in place.

“Well, it’s too awesome of a morning to be asleep.”

“I can’t even remember what happened last night. When did we take a cab?”

Charlie stopped in place, paused the song, and looking at you incredulously.

“Wait, what do you remember?”

“I remember the fashion show, seeing Sam, meeting Cas, but everything else after that is blurry.”

“You really don’t remember _anything_ after that?”

You proceeded to shake your head no, then gripped on the side of it after feeling pain and a wave of nausea. That was a mistake. Note to self: Do NOT move today.

Charlie leaned in, looking at you like it was her sole duty in life to disclose the following words, “Y/N, last night was the best night ever.”

In between girlish squeals of glee, Charlie she proceeded to recap what happened last night while bits of it came back to you. While you were talking with Sam, Cas introduced Charlie to practically all her idols in the industry.

When you made your way through the crowd to meet up with her, she introduced you as the designer of her dress. That part you remember - familiar faces from Charlie’s blog, the biggest names in the industry looking at your dress and judging you as you stood frozen in place. You do remember that part as you’ve never felt so nervous in your life. You tried your best to gracefully pick up another glass of bubbly whatever to deal with the attention. According to Charlie, your dress was the talk of the party, even though it was supposed to be Castiel in the spotlight. But she did attempt to do some damage control and mention that you were Castiel’s protege, to which he was grateful for. That part you don’t remember. After scolding her about that, she went on to tell you that you met your idol, Abaddon, the supermodel.

“Wait, I met Abaddon?” You asked in disbelief.

Abaddon was the supermodel you aspired to design for. She was a powerhouse in the fashion industry, always wearing her signature red lipstick that she could pair with anything and make it look glamorous. There was no doubt that if she wanted to she could make paper bag dresses all the rage.

“Yeah, she came up to you looking absolutely gorgeous,” Charlie mused, a goofy smile on her face appeared for a moment before she gathered her thoughts adding, “and she loved your dress.”

“Hold up - Abaddon, _the_ Abaddon loved my dress?”

Charlie slowly nodded her head, lips pursed, and eyes expectantly awaiting your reaction.

“Ok, you can play the stupid song,” you smiled as you stood up, still a little shaky and exhausted but ready to fangirl with your bestie.

* * *

After a mini dance session with Charlie and a liter of water, it dawned on you how long you’ve been wearing that dreaded leather dress. Definitely long enough for you to feel all kinds of gross. You retreated peel out of the now icky dress to take a hot luxurious shower.

Once you walked back into your room, feeling renewed, you noticed a notification light up on your phone. It was a text from Sam.

**Morning beautiful. Sleep well? What do you think about grabbing a coffee with me? That is if you’re ok with coffee.**

You smiled wide, not understanding why coffee would be an issue for you. You replied:  
_I slept fine. I’m good with coffee, but I thought you model types shouldn’t drink it ;)_

**I can indulge, but I wasn’t sure about you…**

You smirked as you sent the next text  
_Well, I can drink anything I want_

**Yeah, I know, you’re a cute drunk :D  
You good to meet in an hour at the coffee shop across Beech St?**

Your smirk disappeared. Huh? What did he mean by that mean? Sam left the party before you got drunk, didn’t he? When you saw him you only had the one drink - did he think you were drunk then? Noticing how much time you spent pondering, you replied quickly, hoping the lag in response didn’t seem off.

_Yeah, see you there._

You were confused and stood in the middle of your room, looking up to the ceiling as you held onto you phone, strumming your fingers impatiently on the back of it with one hand. Your mind raced, trying to scrounge up any hazy memories of last night. What did you miss? A thought crossed your mind and you stopped strumming on your phone, holding it in front of you instead. There weren’t any other previous messages with Sam so you checked your call history.

You bowed your face down into one of your hands, covering your eyes in defeat when you discovered a call that was logged to Sam in the wee hours of the morning. Not any kind of call - the drunk call, the call you don’t remember a word of.

Fuck! This was mortifying. What could you have said to him in your inebriated state?

Taking a deep breath in and exhaling slowly to calm yourself, you promised to never drink that much ever again.

* * *

“You’re a genius,” Charlie said plainly as you stood in front of the full-length mirror admiring your outfit that you pulled together in less than 10 minutes.

It was clean and casual as you paired your trusty dark wash jeans and red ballet flats with a floaty cream blouse of your own creation, which donned a sheer neckline and sleeves to match.

“Thanks,” you smiled, feeling excited about your coffee date with Sam… uh, was it a date? Or was it just a meeting of old friends? Were you more than just friends? Ugh, you wished your hungover brain wasn’t so quick to question or doubt yourself. But then again, you were out of sorts today.

“I mean, you don’t even look hungover,” she continued as you rolled your eyes at her comment.

After applying a quick swipe of lipstick, you were on your way. It took you a little longer than anticipated to get ready, but thankfully wearing comfortable flats helped you speed out the door.

Once you stepped outside, you looked up questioning the overcast sky that suddenly blocked the sun. Debating whether you should bring an umbrella but deciding to forego it in the name of fashion and laziness. You didn’t want to go back to your apartment and you certainly didn’t want to spend time bickering with Charlie who would probably complain that your umbrella would clash with your ensemble.

By the time you reached the coffee shop there was a chill in the air and the overcast sky transformed to dark grey clouds, threatening a big storm. You hoped the foreseeable rain would pass while you spent time with Sam, drinking something warm, catching up on the years that went by and just staring into each other’s eyes.

Nervous and excited, you opened the large glass doors to enter the coffee shop, actively scanning the room to find Sam but got distracted by a young couple exchanging heated words in the middle of the store. They were bickering loudly, it was making everyone cringe and got you annoyed since they were blocking your path. You tried to slip by the couple, slowly sidestepping around them and the merchandise displays when suddenly you heard a shriek. This was followed by the feeling of hot liquid splashing on the front of your blouse, making you stand frozen in place with your mouth open wide.

What. The. Fuck!?!

You looked up to see a guy leaning to one side, obviously dodging the beverage that was meant for him. Behind him was a girl with an empty cup in her grasp, face red with anger and eyes filled with confusion.

Looking down at you blouse, you saw the remnants of what looked like a mochaccino - fresh milk froth and chocolate shavings on your blouse. At least it wasn’t scalding hot coffee, you thought, desperately trying to find some silver lining in this otherwise horrible mess.

“I’m so sorry!” the girl apologized profusely to which you responded to her politely.

You weren’t going to let this moment ruin you. No, you could fix this. It was just a little stain… ok, no that was a lie, it was a big stain. But maybe you’d get a chance to fix it before you see Sam.

Just then, Sam entered the coffee shop looking flawless like he walked out from a photo shoot for men’s casual workwear wearing jeans and a deep blue  button-up shirt, which looked tailor made to highlight his chest and broad shoulders. It was absolutely unfair. No one should be able to look this perfect all the time. His eyes glossed over the disarray in the middle of the shop and once he met your eyes, he rushed over to you.

“Y/N! What happened?” He asked worriedly as a lock of hair fell in front of his eyes, his body seemingly willing himself to look more sympathetic towards you.

“I-,” you shook your head feeling humiliated. You didn’t know what to say to him now, you felt like an idiot. It felt like one mishap after the next especially since you didn’t know what you said to him last night. You began to feel sorry for yourself realizing that this beautiful man was here to see you. You - an utterly, unglamorous bore. What could you possibly do for him?

The emotions became overwhelming and you bit your lip, beginning to feel it quiver.

No, don’t cry. Not now.

Looking down, you muttered, “I’m sorry, Sam. I thought I can do this but I can’t right now.” You rushed past him and exited the coffee shop.

Sam stood there, stunned as he ran a hand through his disheveled hair, turning around to see where you ran off to.

Rain began to fall from the gloomy clouds but you briskly walked into it and down the street with no destination. You needed to just get away from the embarrassment of making a fool of yourself, yet again. Tears fell from your eyes, mixing with raindrops that collided onto your cheeks. The trickle of weathered sadness soaked your stained blouse. You felt like a complete mess. You crossed your arms over your chest tightly as if trying to hold yourself together.

“Y/N! Y/N! Wait!” Sam beckoned as he ran up to you (damn his long legs giving him the advantage to catch up to you so quickly!). He turned you around, placing his large hands on your shoulders as he held you in front of him.

“Sam, please just let me go,” you implored, not able to look at his face.

“At least let me take you home.”

“I don’t want to go home, I just…” you sighed, shaking your head and closing your eyes as the words spilled out, “I was so nervous last night that I just kept drinking. I don’t remember anything from last night - I don’t remember calling you, I don’t remember what I said. I just feel like I keep humiliating myself and I just-.”

Sam wrapped his arms around you, holding you tight against him. You missed that feeling, burying your face into his chest, being close to him. It made the empty feeling in your chest fill with warmth and the tears ceased. The rain continued to fall, the warm droplets cleansing the sadness away as Sam held you in his arms.

“You’re just having a bad day,” Sam tried to reassure you. “Listen, let’s just get out of the rain and head to my place, ok? It’s close by.”

Still sniffling, you pulled back to tell him that you weren’t sure if it was a good idea. But once you looked up at him, all reason escaped you. Even though you saw him yesterday, you finally got a chance to really look at his face for the first time since college. His hair was longer, slick from the rain, a lock of it clinging to his cheek. His features were more chiseled, not as cuddly and soft as before, not that he wasn’t masculine before but he looked like a real man now. The only thing that remained the same were Sam’s eyes - warm and multicoloured - always making you feel safe. You could’ve stared at him for hours, but the rain broke you from your reverie making your eyelids flutter to avert the droplets of water.

“Ok,” you gave him a small smile and nodded in agreement.

“Good,” He said softly, taking a finger to tip your chin up and lay a quick peck on your forehead. He grinned, adding, “I’ll have you know that I haven’t cleaned up my place, so I promise you the next time something embarrassing happens, it’ll be about me.”

You let out a quiet snort of amusement as Sam released you from his arms, offering you a hand. Placing your small hand in his, the two of you walked through the curtain of rain towards his place, uncertain but hopeful of what awaited you there.


	3. Bad Time to Be In Love

**Summary for the Chapter:**

> After a rough start with your coffee date with Sam, he takes you back to his place and makes a confession to you

**Notes for the Chapter:**

> Written for @torn-and-frayed Songs of Supernatural - Season 1 Challenge. My song was Grand Funk Railroad - Bad Time (To Be in Love). It was so refreshing to not write smut for once. But don’t worry, it will happen soon-ish.

([x](http://out-in-the-open.tumblr.com/post/77302500127/appreciation-of-winchester-genes))

You always appreciated the rain, but only when you were indoors snuggled under a cozy blanket, listening to the ambient sounds of raindrops hitting the window pane. It was only a short walk to Sam’s place from the coffee shop but during your stroll, you discovered a newfound appreciation for being outside during rainy days. The two of you continued to walk down the street hand in hand while the rain continued to fall.  Even though you were getting soaked to the skin, you pace remained unhurried as if the rain didn’t exist.

“You know, I had a rainy photo shoot last month,” Sam mentioned casually.

“Oh yeah? What for?” You asked.

“Funny enough, it was for Castiel’s trench coats,” Sam chuckled, “the one with the improved waterproof fabric to keep you bone dry.”

You laughed, “That’s funny… You know, I don’t think I’ve ever spent so much time out in the rain, no umbrella, and not immediately rush for cover.”

“Feels nice, doesn’t it? Just being in the moment.”

“Yeah, it’s…”, you sighed in satisfaction, “liberating like I have nothing to hide.”

Sam’s hand tensed slightly prompting you to glance at him, “Everything ok?”

With a quick clear of his throat, Sam nodded, “Uh, yeah, my place is at the next corner.”

The stormy skies darkened and you could hear thunder rolling in the distance. It was a good thing you reached Sam’s building then. As much fun as it was to stroll through the rain you were happy to retreat somewhere quiet and dry before it got worse.

When Sam approached his door, he paused, glancing down at you with an amused smirk before bringing your hand to his lips. He gave your hand a chaste kiss before letting it go to unlock the door. You were smitten by the sweet gesture, not just at the kiss on your hand but how good he’s been treating you this entire time.

_Entire time?_

Who were you kidding? It wasn’t even 24 hours since you bumped into him for the first time in years and you were just… was it possible you were falling for him this quickly? Ugh, no, get a grip. It’s just the situation and you’re romanticizing your memories of Sam back in college to present day Sam. You gotta live in the now, Y/N, and right now you are standing beside a gorgeous man, a model, who was being nothing but perfect to you. You were at his door, and about to be alone with him. Living in the now was good.

Once you entered his apartment you immediately noticed how quiet it was, only the sounds of the rainstorm echoed. The steady tapping of the rain against the windows was actually quite soothing but as soon as you looked up, you froze, your clothes dripping onto the entryway mat by the door, as you soaked in the view.

If people’s homes were a reflection of who they are, then you were flummoxed by Sam’s apartment. You admit that you didn’t get a true sense of who he was years ago since he shared a place with his brother, but you really thought you had him figured out. It was a spacious loft apartment with tall ceilings and big windows. There were a collection of photos on one wall that looked as if it were meant to be clustered, a trendy decor style, but empty gaps flooded the spaces between. It just seemed like a lot of space, a lot of uncluttered space, in his loft for just him. If not for the opposite wall that was lined with books, so perfectly Sam, you wouldn’t have guessed that he lived here.

“Wow,” you marveled, still taking everything in.

“Yeah, it’s all mine. No more sharing with my brother, which means I have a drawer full of condoms now,” he announced with a jest.

Your mouth parted in surprise, hoping he was referencing what happened years ago in college but even still you weren’t sure what to say.

“Sorry, that was inappropriate,” he cringed, shaking his head.

“No, it was funny,” you shrugged, finding some playful confidence as you looked at him with a shy smile, “and something I’ll keep in mind.”

Before Sam could respond an unexpected loud roar of thunder made you jump into Sam and grab onto his sleeve. Instinctively, he wrapped his arm around your waist, holding you steady as if you were a delicate vase about to be tipped over.

You breathed out an apology as you shook your head down with a nervous laugh, “sorry, I guess my nerves are just completely shot today.”

Sam still held you, and you were afraid to look up at his face, afraid that if you met his eyes then he’d let you go. Even though the two of you were absolutely drenched from the rainy walk, you didn’t feel cold anymore, you felt comfortable and safe in his arms.

You relaxed your grip on his shirt, your fingers spreading out on his bicep feeling the firmness underneath the wet fabric that clung to his muscles. Slowly, you lifted your head, eyes trailing from Sam’s wet shirt to his still glistening throat that was hypnotizing. You only had the sense to look up to his face when you the bobbing of his Adam’s apple as he swallowed hard. When you finally met his eyes, Sam had a look of longing, his pinks lips parted.

“It’s ok,” he breathed, his hands caressing your back, “I got you.”

Time seemingly slowed in that moment as Sam leaned in, pausing to dance his eyes around your face, flitting between your eyes and your lips as he got closer. Your eyes remained fixated on his pink lips, waiting and wanting, not quite believing this was going to happen. You closed your eyes when Sam was mere inches away, just a second of hovering hesitation before he closed the gap.

He pressed his lips to yours and you sunk into the kiss like a warm, luxurious bath. It was soothing and soft, making you hum, which prompted Sam to hold you tighter against him. Kissing him was better than you remembered if that were even possible. Although, it felt good to be kissing him and to be closer to him again, the feeling of your wet clothes was distracting you.

There was something about the kiss and the free-spirited feeling you had from the rainy walk that sparked a newfound confidence in you. You promptly broke the kiss, pushing Sam away, and stepping backward with a seductive smirk. His face remained dumbstruck in a hypnotizing trance as you peeled off your wet blouse over your head, hearing it the ground with a wet thud.

Sam’s eyes widened trailing up and down your body, now only clad in a wet bra and jeans.

“I don’t want to get hypothermia,” you teased as you reached your hands to unclasp your bra.

“Stop,” Sam blurted, his hand on his forehead covering his eyes. “I…” He shook his head as if fighting with himself as he stood in place. “I’m sorry, I feel like I need to tell you…”

In those few seconds that Sam trailed off, you felt devastated, a chill in your body, not only from being practically topless but also while several dozen questions raced through in anticipation.

_What does he need to tell you? Tell you that he didn’t feel anything when you kissed? Tell you he hates your body?Tell you a lame excuse to let you down easy because he’s just realized he’s a fancy model and can do better than you?_

He removed the hand from his face before confessing in a sigh, “I just got out of a long-term relationship.”

“Oh?” you managed to squeak out, arms crossing to cover your chest, fully thinking that he was giving you the excuse route.

“It’s complicated,” he explained, rubbing the back of his neck with one hand.

Your lips pursed and parted before you spoke, trying to give him the benefit of the doubt, “W-we don’t have to-”

He interrupted placing his warm hands on your bare shoulders, “please don’t think it’s not like I don’t want to,” he rubbed circles on your shoulders bringing some warmth back, “I just don’t want to treat you like a rebound or anything. It was so good to see you last night and I don’t want to mess anything up.”

Now you knew he wasn’t giving you an excuse. This was the same Sam you knew, feeling like he needed to lay all the cards on the table giving you an out if you wanted. Any other guy would’ve taken advantage of you without a second thought. But Sam, he always put the needs of others’ above his own.

You took a deep breath to collect yourself.

“How about you let me borrow some dry clothes and we can talk? I do believe I was promised a coffee,” you proposed with a small smile.

Relief was evident on his shoulders that relaxed as a huge grin appeared across his face.

“Sounds good.”

Sam led you the bathroom, handing you some towels and a set of clothes, while he headed to his bedroom to dry off and get dressed.

It was a pretty spacious bathroom, lots of counter space and a big shower with one of those rainfall shower systems that was not at all appealing now.

Looking into the mirror, you cringed noticing your drowned rat look. After cleaning up the smudged makeup on your face, you were craving a hair dryer to prevent your hair from getting flat and frizzy. You searched the cabinets underneath the sink and found a hair dryer on top of a box labeled _Jessica_.

You froze.

 _Jessica_. That had to be his ex…and this box was her stuff. There were so many questions that raced through your mind that were quickly silenced when you shut the cabinet door.

You had a nagging feeling to text Charlie with details but it seemed like now wasn’t the right time. No, you were not going to deal with this now. Focus Y/N. Right now, all you need to do is get dry and talk with Sam. If he wants to tell you about Jessica, then let him. Besides, you’d have a recap with Charlie with details regardless.

Decidedly, you took a fluffy towel to dry off to the best of your ability, being extra careful with your hair. You actually felt proud of how you styled your carefree tresses, making it look like you just spent the day at the beach instead of in a downpour. When you unfolded the clothes Sam put aside for you, you were tickled to see an oversized shirt and sweatpants, which were a loose fit but pretty comfy nonetheless.

Finally leaving the bathroom, you padded down the hall only to find Sam in the kitchen tinkering with the coffeemaker. You crossed your arms, leaning against the doorway as you quietly studied him with amusement. His hair was perfectly piecey and tousled with a slight soft curl at the ends that you wanted to run your hands through. His outfit was similar to yours, a simple gray sweatshirt and black sweatpants, only they fit him better. It was only a menial task, making coffee, but seeing his perfect profile as he concentrated made him seem so suave.

“Hey,” you murmured, making your presence known.

Sam’s face lit up instantly once he saw you in the baggy outfit, his dimpled smile making your heart flutter. “Hey, coffee is on its way. Why don’t you take a seat on the couch?”

“Okay.”

You made your way to the black leather L-shaped couch that was situated behind a matching coffee table and home entertainment unit that flaunted a flat screen TV, speakers, and a multitude of electronic gadgets. As you sat back on the couch, something on that sleek cabinet stood out to you, something old and oddly familiar.

Your eyes widened in realization.

“Oh, my god! Is that the cassette deck?” you exclaimed, jumping off the couch, and kneeling at the clunky, silver-faced unit that you fondly remembered from college.

“Yep, same one,” his deep voice called out from the kitchen, overpowering the sounds of coffee brewing.

“Does it still work?” you shouted.

“Yeah, I listened to something last night.”

Without any thought you pushed down on the play button with a considerable force, remembering briefly that electronics back in the day were not as fragile as they are now. The sound of classic rock began mid-chorus

_I’m in love but I must have picked a bad time to be in love_  
_A bad time to be in love_  
_A bad time to be in love_  
_A bad time to be in love_

You instantly regretted pressing play, feeling awkward as if you opened his diary or something. Music choices can be so personal sometimes and for you to discover that he was listening to this particular song… it could mean everything and it could be nothing. There was a good chance that you were reading too much into the situation. But that couldn’t stop you from questioning whether Sam listened to it before or after your drunken call to him last night.

Just as the song faded out, you were distracted by a warm aroma entering the room. Turning around, Sam was already halfway to the couch, armed with cups of hot coffee.

“Oh, my savior has arrived,” you mocked, truly grateful for a hot beverage to divert your concerned mind.

“I try my best,” Sam teased, as he placed the mugs on the table before sitting down on the couch.

“I was talking to the coffee,” you quipped as you got up to sit next to him.

Holding the warm mug, you looked down at the coffee, it was brown but not too pale as if Sam only put a splash of cream in your coffee. But he didn’t ask how you….wait, did he really remember? Trying not to get overwhelmed by that fact, you took a sip of your coffee and got preoccupied with the mellow flavor. When you swallowed the liquid, you got lost feeling the warmth descend down your throat.

You didn’t know how much you needed that sip of coffee but somehow you found the nerve to get some answers.

“So… how long have you been single?” You questioned, trying to keep a composed tone.

Sam’s eyebrows  raised in surprise at your forwardness. “Wow, just getting right to it.”

You shrugged in reply as you continued sipped on your coffee, holding the mug in your two hands.

“Uh,” Sam sighed, running a hand through his already tousled hair and looked down at the coffee table as he spoke, “just a little over two months now.”

“You doing ok?” you asked, concerned.

His lips curled up at the sides, “Yeah, I mean, it’s not the end of the world but you know I’ve got good days and bad days… uh, you sure you’re ok talking about all of this?

“I can handle it, I’m a big girl and if anything, I’m still your friend. We can talk about you and your ex if it helps… and if you’re afraid of it getting weird, we don’t even need to say her name. She’ll be a fictional character, _She Who Must Not Be Named_.”

Sam snickered in amusement, “Yeah, because calling her that wouldn’t be weird.” With a long breath in, he rubbed his hands on his thighs, finally exhaling, “Ok… well, in this short version of the story let’s call her X for now. I met X at a photo shoot when I was starting out and we kept bumping into each other. Eventually, we got to know each other and things just clicked. We dated for a while then after that we got a place…” his eyes drifted downwards, “but then throughout the years, life just got in the way. I’ve been struggling with my career and she kept traveling for work. Didn’t think much of at the time, it was just what we did. Then one day, about two months ago, X left for good. I guess I didn’t even realize it at the time but we grew apart… whatever we had was just gone. But I think what really hits me is that I remember the moment when it was really over when it felt like hanging out with a roommate instead of a girlfriend, but I just brushed it off. I was just in denial.”

There was a pain in his eyes that you wished you could take it away. This was no regular breakup that could be solved with a pint of Ben & Jerry’s. This was a life change - having someone you care about thinking you could always count on them to be there in the future, just suddenly disappear.

“I’m so sorry, Sam,” you whispered, reaching out to place your hand on Sam’s, giving him a reassuring squeeze. It was not much, but it was all you could do.

Sam’s lips turned up into a smile at the sight of your hand on his.

“I’m ok, though, there have been a lot of good things happening since the breakup. For instance, I’ve got more space for stuff like the cassette deck that X always thought was an eyesore.”

You giggled, making Sam’s dimples appear as he continued his list.

“I’ve gotten a chance to say yes to modeling jobs that I would’ve said no to in the past. Then at one of those modeling jobs, I met a beautiful woman who enjoys calling me in the middle of the night to whisper sweet nothings.”

“What?!” you blurted, immediately flustered and covered your hands on your face.

Sam laughed, “I’m just joking, Y/N. You were nothing but cute on the phone, nothing scandalous happened, I promise.”

You removed your hands from your face to see his face soften, suddenly making you shy.

“Honestly, though, you have no idea how good it was to run into you.”

Darting your eyes downwards, you replied, “I’m glad I ran into you too, Sam.”

He shifted closer to you on the couch, his head angling to catch your attention, “Is it weird if I tell you that it feels like the universe wanted to give me another chance with you?”

You looked at him dumbfounded at his ability to be so perfectly corny that you wanted him even more.

“And I realize that the timing is just horrible - it’s been years since we’ve seen each other and I’ve got baggage with this breakup. But not seeing you and not telling you this feels like a mistake.”

There he was again, the Sam you knew, letting you know the whole story and giving you the upper hand on what to do next. It all felt a little overwhelming.

“Well, then maybe we should just go slow… talking, texting, emailing… just get to know each other and be friends, for now. Lay a foundation and if it doesn’t stick then neither of us gets hurt since we didn’t rush into anything.”

“You’re right, you’re completely right, Y/N,” Sam agreed, looking at you contently.

“What?” you questioned him when his stare went on longer than expected.

“Just appreciating the view,” he murmured.

“Well, stop it, your coffee’s going to get cold,” you smiled, shaking your head, and straightening up in your seat beside Sam.

There it was - an agreement settled on how the two of you would take it slow. But as you each sipped on your coffee beside each other in silence, there was a mounting tension. You could feel Sam’s eyes on you when you weren’t looking and you were certain he could feel your eyes on him.

Chugging down the rest of the coffee, you placed the mug on the table and faced him.

“Ok, am I crazy or is there a tension that needs to be dissolved here?”

Sam looked at you intently, “Yes, I feel it too. Can I… can I kiss you one more time?”

“Yeah, one kiss won’t hurt,” you agreed enthusiastically, “just to seal the deal, right?”

“Right.”

The excited smile on your face faded quickly as you readied yourself to feel Sam’s lips on yours once again. He reached out his hand to cup your face, making you close your eyes, patiently waiting to be kissed…

_“I’m walking on sunshine, WHOA!”_

Goddammit, Charlie!

The ringtone of the beloved and dreaded song emanated from your purse by the entryway table, ceasing the heated moment.

“Is that your phone?” Sam asked quizzically as he pulled back, his head looking towards your purse.

“No, that’s my soon to be dead roommate,” you grumbled.


	4. Lip Blocking

**Summary for the Chapter:**

> After Charlie interrupts an epic moment, Sam offers to help you out with your career aspirations

**Notes for the Chapter:**

> I missed writing this series so much. Things are going to change in a good way in the next part. Feel free to send me any feedback. I’d love to hear from you!

* * *

([x](http://canonspngifs.tumblr.com/post/151385641287/livingthegifs-dont-wait-up-requested-by))

Ugh.

You loved Charlie. Truly. She was your best friend, she was an awesome roommate, and she’s always been there for you… even in those moments when you wished she didn’t exist, like now. Charlie had the worst timing for calling you in the middle of what could’ve been an epically romantic moment between you and Sam.

If only the two of you didn’t get interrupted by the muffled tinny echo of a pop chorus, that inevitable kiss would’ve been so perfect.

But now that moment was gone.

“I’ll just be a minute,” you excused yourself, speeding towards the kitchen with your purse in hand, the 80’s tune still blaring from your phone. All the while you fully intended to change your ringtone, and kill your roommate when you got home.

You answered the call with a quiet hiss, “Charlie, this better be good since you’re a dead woman.”

“What? _You’re_ the dead one!” she replied accusatorily. “Where have you been? You disappeared completely, not texting me and not reading my texts,” she huffed before continuing in a calmer tone, “I’m just checking in, are you ok? How’s the date?”

Oh, crap.

You pulled the phone away to check your texts… sixteen texts from Charlie all ranging from a simple “ _so how goes it?_ ” to “ _Y/N I STG DO NOT PLAY AROUND! I’M GETTING WORRIED. CALL ME!!!_ ”

You immediately felt like a good-for-nothing heel. The two of you established a set of rules before heading out to your first party in college as roommates, just trying to look out for one another. It became a standard safety arrangement that followed a three-step process: 1) text each other to check in, 2) call if there’s a problem, and if all else fails 3) gather the search party. There’s never been a need for the third step but this is the first time you’ve ever failed to text her in the decade you’ve known her. It’s also been ages since you’ve been on a date that you forgot all about the arrangement. Major oops.

“Oh Char, I’m soooo sorry,” you winced, “I totally forgot. I’m safe but, uh, slight change of plans,” in a whisper you added, “um, I’m at Sam’s place right now.”

“Dude!” she gasped, “that’s… wow…ohmygod, was I cockblocking you?”

“Nonono, nothing like that more like, um,“ you questioned each word as you spoke, “lip… blocking?”

“Huh?” she blurted, “do you have pants on? I hope you wore that red-”

“Charlie,” you interrupted, not wanting to lengthen the conversation, “I gotta go. I’ll fill you in later, ok?”

“But-”

“Bye!” you ended the call and immediately put your phone in do not disturb mode. You left so many questions unanswered for her, it was inevitable that she’d text you non-stop.

You took a deep breath to compose yourself before leaving the room to face Sam again.

Upon entering the living room, he turned to you, eyebrows raised in question, making a slight wrinkle on his forehead. His adorably concerned face made your lips quirk up at the corners.

“Everything ok?”

“Yeah, everything’s fine,” you explained as you sat next to him, “Charlie and I have a safety texting thing we do but it slipped my mind and she got worried.”

“Well, I can see why she’s so concerned, I am pretty dangerous,” he teased.

You smiled wide, “we just look out for each other.”

“No, I get it,” Sam nodded, “Charlie seems really cool.”

“She’s the best,” you spoke fondly, “you, uh, actually owe her a big thanks. I only went to the fashion show because I was her plus one.”

Sam’s dimples made another appearance, “I’ll make a note of that. Hey, maybe for the next show you can get an invite and a plus one for yourself.”

You scrunched up your nose, shaking your head in response, “highly unlikely. I’m a nobody in the fashion world.”

“You’re just unknown, for now,” he clarified with optimism, “you’ve got the talent, I mean, you heard Cas last night and let me tell you that things move incredibly fast in this business.”

It was so flattering to hear Sam be so uplifting like he actually believed you could make it in this industry. For a fleeting moment you believed it too, his dreamy outlook was soon crushed by your logic as you reasoned with him, “That may be, but I don’t have any real industry experience, Sam. It’s all about who you know. I just gotta get my foot in the door and be more than a comment at an after party.”

His eyes shifted, pondering. He looked back amused, his lips moving in and out of an upside-down smile before he spoke, “Don’t take this the wrong way, but you know me. I mean, I’m not a huge deal or anything but I have some contacts.”

“Are you sure?” you questioned him with uncertainty.

“Come on, I _know_ people who _know_ people. Please let me help you out, Y/N. I owe you that much.”

You furrowed your brows, unsure what he meant, “What do you mean, you owe me?”

“Well”, he looked down as a shy smile appeared on his face, “everything I have right now is partly thanks to you. Not just the encouragement but…”

He ran a hand through his hair, teasing at the ends as if it was part of the explanation and immediately you understood what he meant.

“I don’t know how much you remember about that night-”

You couldn’t wait for him to finish his sentence, knowing exactly what he was going to say. In an instant, you shifted closer to Sam, reaching out a hand to cup his face and looked at him in awe before you smiled wide, “Because I told you-”

“Yeah”, he replied, reciprocating the smile as his hand reached up to encircle your wrist, the pad of his thumb gently brushing the back of your hand that touched his face.

It was that moment you crashed your lips to his, an overwhelming feeling of being captivated by Sam. There was a joyful purpose in the kiss - the joy that you may have had a hand in his success, that he was willing to help you out to achieve your own dreams, and that he was here with you - this part of your life that you’d never thought you’d get back again. The moment felt perfect as Sam’s lips moved against yours, smiling into the kiss, perhaps feeling the same joy you were.

Not wanting to overstep your bounds like before, you pulled back from the kiss, one hand fidgeting in your lap and the other grazed your swollen lips.

“Sorry, I just…” you giggled, “because I said I liked your long hair?”

Sam blushed, chuckling, “It’s kind of my signature look… So is that a yes? You’ll let me help you?”

You simply nodded, “Well, we agreed - one last kiss to seal the deal, right?”

Sam reached his hand over yours, squeezing it.

Right then, the slate was clean. Any previous embarrassments, any lingering hangover or interruptions you had up until that point didn’t matter. The universe seemed to finally be working in your favor - re-introducing this beautiful man into your life who was going to help you get a job doing what you loved.

It would just take some time for the two of you to get to know each other again. Taking it slow and steady.


	5. Fashion Moves Fast

**Summary for the Chapter:**

> Sam’s connections in the industry lead to you to a position working for one of the hottest fashion magazines

**Notes for the Chapter:**

> This is a completely unrealistic portrayal of securing a real job but I hope y’all enjoy the fantasy. How are y’all enjoying the slow burn? Feel free to leave feedback/comments. I’d love to hear from you!

Sam was right. Fashion moves fast.

It was only one month since Sam told you he’d help you out but things moved at a thrillingly fast pace that you weren’t prepared for. Sam completely underestimated his pull with whom he knew in the industry. He had built up so much goodwill and was such a charmer that it took less than a week to get you a job.

Sam managed to pull some strings with the assistant to the editor in chief at _Crossroads_ , the hottest fashion magazine there was in the industry. They were known as the source for declaring what is in and what isn’t. They have announced new trends and brutally cut down red carpet fashions. Some may say their work is demonic, but sometimes that was the nature of the fashion industry.

Once Sam was able to speak to Crowley, he intended to secure an interview for you. Miraculously, even though you lacked any experience, somehow your association with Castiel and Charlie’s blog convinced Crowley to hire you and Charlie without an interview.

It was unreal, you and your best friend were now full-time employees at _Crossroads_. Even though the two of you worked in the same office and lived together you hardly saw each other. Charlie was a digital marketing assistant, using her expert computer skills to blog and keep track of where the who’s who would be. She was always on the go covering photo shoots, the latest runway shows, and seemingly every fashion event. The only time she came home was to shower and sleep. But it wasn’t like you didn’t keep in touch, the amount you texted each other skyrocketed and you lived vicariously through her social media posts, like the rest of her followers.

In comparison, you lived in the magazine’s fashion closet as a wardrobe assistant. Your days were spent surrounded by fashion - organizing outfits and accessories for photo shoots, coordinating samples from designers, pressing hemming, sewing… to anybody else, it would’ve been boring, but for you, every day was a thrill.

Being in the fashion closet all day meant you didn’t interact with a lot of people at _Crossroads_. Not that you were a total pariah, you had acquaintances and worked well with others, including your boss, Jody, who had a no-nonsense but motherly attitude towards you. But you never ended up going out on any events that you overheard folks chatting about the morning after in the elevator.

Actually… maybe you were the pariah? It didn’t bum you out, though.

The one person you could always count on in the office was Kevin, Crowley’s executive assistant since he was kind of an outsider too. It seemed that people only spoke to Kevin when they wanted to get access to Crowley, who was unrelenting with his schedule. Kevin was able to see right through all the fakery when coworkers try to suck up to him, it’s why he was so good at his job. It’s one of the reasons he befriended you, knowing you were one of the genuine people he could trust in the office.

* * *

It was a quiet day for you matching accessories for photo shoots next week. Jody left early, giving you fabric swatches and detailed notes on what accessories went with which swatch. You found it odd not being able to even see what item you were matching it to but didn’t question it. Not wanting to seem like a newbie, you got lost in the closet with determination to choose the perfect accessories. Just when you were attempting to find a scarf in just the right shade of white to match a royal blue, you heard a friendly voice in the distance.

“Y/N?” Kevin called out, his voice getting louder as he entered the closet.

“In here, Kev! Are you heading out for a 3 o’clock latte?”

He stared at the sea of scarves, then looked at you, perplexed, “It’s not 3, it’s 7. What are you still doing here?”

“Crap,” your eyes widened, rushing to clean up. This often happened to you since there were no windows or clocks in the closet, you just got lost.

Kevin scurried in to help you tidy up the scarves.

“You don’t have to do that,” you tried to brush him off.

“If I don’t you’ll never get out of here. Besides, it’s Friday and it’s time to catch up.”

You gave him a friendly knowing smile while you cleaned up, knowing the task wouldn’t be pleasant as you heard this week’s gossip. Kevin that had all the juicy details, which suited him just fine. It was a delight for him to finally have someone he could confess these secrets to that he trusted. You thoroughly enjoyed hearing the latest inside scoop around the office. It wasn’t anything like Charlie’s gossipy sessions, which you so dearly missed, but it still kept you in the loop.

Right when he was talking about one of the girls from accounting hooking up with the IT guy, you heard the faint buzz of your phone on vibrate. You often switched your phone to silent at work, it seemed like ages since you’ve actually heard a ringtone from your phone. Hurrying towards your tote bag you scrambled, diving in your hands to take out your phone, spilling half the contents of your bag on the floor in the process.

Kevin rolled his eyes, moving towards the floor to help pick up your stuff.

“Hey Sam!” you answered eagerly.

Sam was in California for the week, doing some photo shoots with his brother. In the past month, he’s been on multiple photo shoots on location. The two of you tried your best to keep in touch, but even still it was trying. Pretty much every call was a quick ‘hi’ and ‘goodbye’, the timing was always off not leaving room for any heart to heart chats. The silver lining was that you’ve been too busy at work to truly miss him but these calls made it difficult to do so.

“Y/N! Hey, it’s good to hear your voice. What are you up to?”

“Ummm…” you trailed off, not able to come up with an excuse.

Sam sighed, “don’t tell me you’re still at work.”

“Pfft, no,” you decided to tell a white lie, “I’m hanging out with Kevin.”

“Sam, she’s been stuck in the closet all day,” Kevin hollered to the phone’s direction to which you gave him the biggest bitch face.

Sam laughed, “Oh, you are so busted.”

“I was just trying to find a scarf,” you defended yourself before deciding to flood him with questions. “Anyway, how are you doing? Have the photo shoots been good? How’s Dean?”

Sam replied listing out his answers, “I miss you, photo shoots have been great, and Dean’s the same old grump.”

Shortly after you overheard Dean in the background calling out _‘I heard that’_.

You smiled, requesting completely unashamed, “Say that first part again.”

Sam paused. “I miss you,” he said with a smile and a sincerity in his voice that made you swoon.

“I miss you too,” you cooed.

There were noises on his end that you recognized as the photo shoot getting underway.

“Uhh, I gotta get going now, but I’ll see you tomorrow night?”

“Can’t wait,” you chirped.

“Can’t wait to see you too. Bye, Y/N.”

“Bye,” you whispered.

After you ended the call you dropped your phone onto carpeted floor, sighing audibly, completely indulging in the warm, fuzzy feeling.

“You two are disgusting,” Kevin muttered with a smirk.

“I know,” you grinned as you finished smoothing out the last of the scarves only to turn and see Kevin still sitting on the floor surrounded by the contents of your bag. He was hypnotized staring at book… your sketchbook.

“Hey, that’s private!” you exclaimed, rushing to snatch the book from his hands and clutching it to your chest.

“Sorry, it fell open a page and I couldn’t stop looking,” he apologized. “Y/N, your designs… they’re amazing. Have you showed them to anybody? Jody?”

You violently shook your head ‘ _no_ ’.

“You know, I can set up a meeting for you with Crowley-” he began to suggest.

“No!” you blurted loud enough to make Kevin jump. Taking a breath you explained, “Kevin, I’ve only been working in this industry for about a month now. I still have a ton of stuff to learn. The last thing I want to do is test my boundaries or burn any bridges. I-I don’t even know if I have bridges to burn at this point but I don’t want to find out. You know?”

“Yeah,” Kevin nodded in understanding before smirking, “Wow, Sam was so right about you. I had my doubts but he really knows you.”

“What do you mean?”

Kevin began to confess that when Sam first contacted him to get a meeting with Crowley, he spoke highly of you mentioning your incredible talent but that you lacked confidence and experience. At first, Kevin thought Sam only wanted to help out a girl that he had the hots for and after meeting you, he knew you were a good person. But Kevin had no idea what you could really do until he saw your private sketchbook.

“Seriously, Y/N, I see a lot of stuff people want to get through to Crowley that aren’t even a fraction to your designs. Say the word when you’re ready and I’ll set up the meeting,” he assured you.

“Thanks, Kev, I really appreciate it.”

A comfortable silence fell between you two as you tossed everything back in your tote bag.

“So… how long have you known Sam?” you asked, curiously.

“Ummm, a few years,” he replied, “I’ve known Sam and his brother long before I ended up working with Crowley.”

“Hmmm,” you acknowledged, trying to be nonchalant, “So, do you know Jessica?”

“Nope. Nope, I’m not doing this,” Kevin chuckled adamantly, he was already onto your line of questioning, taking his jacket and leaving the room.

“Come on Kev, I’m curious,” you called out, stuffing your arms with your jacket and tote bag, following him towards the elevators.

He remained silent and undeterred as the two of you stood in front of the elevators.

“Fine,” you announced, admitting defeat to finding out any gossip on Sam’s ex. “Anyway, we deserve a drink.”

“Couldn’t agree with you more,” he said, stepping forward as the elevator doors opened.

“Oh, and Kevin, because you busted me? You’re buying.”

Kevin scoffed a brief ‘ _hey_ ’ that was perfectly timed with the ding of the elevator doors closing.


	6. Ignoring It

**Summary for the Chapter:**

> While on a photo shoot Sam ponders his relationship with you. When he sees you he decides to take things to the next level.

**Notes for the Chapter:**

> If you can’t tell from this fic, I’m craving chocolate, having a sweater crisis and enjoying listening to a lot of classic rock. Feel free to send me any feedback. I’d love to hear from you!

([x](http://awkwardsamw.tumblr.com/post/152729993778))  
  


The warmth of the afternoon California sun by would’ve been enjoyable if it weren’t for the fact that Sam was wearing multiple layers in a three-piece suit. It was yet another photo shoot for Castiel’s menswear, the designer wanted to pair up the Winchester brothers in a new campaign to showcase his suits from coast to coast, sort of an all-American road trip. Each shoot went smoothly, but the heat was proving to be troublesome to the model duo as the glow of the heat quickly turned to dripping perspiration, much to the frustration of Gabriel, the photographer.

“Ok, we got to get these guys dry again,” Gabriel shouted, annoyed with yet another interruption of sweat appearing upon the brows of his models, “Castiel, explain to me why we’re not using fans to keep the guys cool? I’m fighting to keep the lighting here but the rate we’re going now-”

Castiel interrupted in a gruff voice, “They don’t need fans.”

“They. Are. Sweating. Your suits are making them sweat,” Gabe explained.

“I’m wearing one of my suits right now and I don’t sweat under any circumstances,” Castiel replied stubbornly.

Sam and Dean walked by the bickering photographer and designer, making their way to the makeup area. Dean already peeled his jacket off and was loosening his tie while Sam immediately reached for his phone and sat down. He often checked his messages whenever he got a break to see if you had sent him anything.

Dimples appeared on his face when he saw the notification that you sent him a photo. It was a selfie of you holding up a martini glass in your hand and smiling with the caption “nothing like a free drink from a friend who threw you under the bus.”

The goofy, carefree grin on Sam’s face captured his brother’s attention. He didn’t even sense when his older brother was peering over his shoulder.

“Cute,” Dean observed, startling Sam.

Sam looked back over his shoulder with an annoyed frown that instantly melted away once he quickly looked back at your picture.

“Yeah, she is,” Sam agreed.

“It’s good to see you getting over Jess,” Dean mentioned as sat in his makeup chair.

“Dean!” he chided.

“What? We can’t say her name out loud?” Dean scoffed defensively, “Come on, tell me about what’s going on with you and Y/N, if I’m allowed to say her name.”

Sam huffed in annoyance, before looking back down at your photo whimsically.

“Y/N and I are… We’re… she’s…” he trailed off, the smile on his face reduced to a look of confusion at how to describe your relationship.

“She’s pretty but a horrible selfie taker,” Gabriel interjected looking over Sam’s shoulder, “that lighting does her no favors. I can make those sweet sugar lips look amazing, you know, just get me in a room with her and-”

“Hey!” Sam barked as he stood tall turning to the smug photographer, jaw clenched and nostrils flared.

Gabriel was unperturbed, turning to Dean, and motioned his head towards the chest heaving giant. “What’s with him?”

“I think the term is… _it’s complicated_ ,” Dean explained, gesturing finger quotations in the air.

Gabriel stepped towards Sam, tipping his head up to search the anger in the model’s face with eyes full of judgment. The confident photographer didn’t budge and Sam proud stance faltered, his face softened to one of annoyance. It was then that Gabriel spoke, drawling out,“You’ve got it bad, my friend. Decide who this girl is to you and let her know soon. Don’t waste her time.”

Sam rolled his eyes as Gabriel walked away, sitting back down and stubborn to let the honey-eyed photographer’s words.

“Y/N is… she’s the one who… she’s…” Sam was still trying to find the words to explain to his brother as the makeup artists proceeded to do their work, blotting the sweat off his brow.

“Sammy, maybe she’s the one,” Dean stated plainly.

Sam remained silent and stoic in his seat, unmoving as the thought raced through his mind.

_The one? Could Y/N is the one?_

But that’s ridiculous, the two of you have only been dating for a month and it’s so soon after Jess, isn’t it? At least it felt like it for Sam.

The One.

Sam continued to ponder the thought. He couldn’t deny that everything felt like it clicked when he was with you. There was an understanding and mutual admiration, like the two of you have been together for years even though it’s only been a month.

But being away on all these photo shoots, it meant that everything was pretty much at a standstill, especially physically. The physical aspect of your relationship? Well, Sam could base it on the last time you kissed. He did enjoy the feeling of your soft lips against his like he belonged there. He wondered, though, sexually, how compatible the two of you were now? It was only one-time thing years ago… and you didn’t exactly do the deed. Thinking about the memory brought a blush to Sam’s cheeks.

The One? The question was too much, too soon. He’d let it go for now.

But Sam was certain about one thing. He couldn’t wait to see you when he got home.

* * *

There was a bounce in your step as you walked to Sam’s loft, carrying a bottle of red wine and a box of chocolate, humming a version of _Walking on Sunshine_. You were in a happy mood despite the wintry chill in the air. Sam was excited to invite you over for dinner at this place, finally back home with no travel plans for a while. You were planning all week what to wear and even had a backup plan all ready in case a rogue cup of coffee would get thrown your way. Never say never.

No, you were convinced that nothing was going to ruin this evening as long as you got to see Sam again.

When you arrived at his door, you took a second to restrain yourself before lightly knocking on his door several times in succession. He promptly answered, greeting you with a simple _‘hi’_  and your breath hitched at the sight of him. Sam looked better than you remembered - his skin slightly tanned, his hair had sun-kissed highlights with a soft curl at the tips. His face was beaming at you as if he brought the California sun back just to warm you in this moment.

But what really took your breath away was his outfit. Sam looked devastatingly handsome in a classic sweater-shirt combo. At his neck, the collar of a white shirt peaked out from the fabric of the sweater that draped over his body to the narrow of his hips. The preppy fit made him look both broad and slim. How was it possible for him to look sexy wearing extra layers of clothing?

Your eyes widened once you realized the color of his sweater was a deep wine red. Looking up at him with your jaw dropped, you broke into a fit of giggles.

Sam tilted his head like a confused puppy, furrowing his brows in confusion like he missed the joke and needed an explanation.

“I’m sorry, I need to show you something,” you grinned, pushing the bottle of wine and box of chocolate into his hands and entered the loft. Swiftly, you removed your pebble gray peacoat jacket to reveal your sweater dress in the same color.

Walking back to him, you did a quick runway turn before you declared in delight, “The exact shade of red! What are the odds?”

You stood in front of him giddy at the pleasant surprise, not waiting for him to respond before taking the wine and chocolates from his hands and headed to the dining table that was already lit with candles.

Sam admired you as you walked away, admiring how the sweater dress hugged every curve of your body. He fully appreciated the color of your dress was the same as his sweater, not just for the novelty of it but he didn’t have to imagine what it would look like if you wore his clothes - again.

“A perfect match,” he whispered to himself.

* * *

Dinner was simple, not much attention was paid to the food as the two of you dove right into a conversation about what happened in the past week. You chatted about upcoming photo shoots you were prepping for, a bit of office gossip, and a mention of interesting fashion trends you’ve seen online. Sam playfully complained about the photo shoot in California, about how the sun was too hot before going on about how the photographer gave him a hard time.

“I’d love to meet him,” you mentioned.

“Who?”

“Gabriel,” you clarified, “every shot he takes looks amazing like he’s playing tricks with the lighting somehow. I used to take a lot of photos for Charlie’s blog and I always wanted to learn how to take better photos, you know?”

Sam’s mouth tensed at your comment, but in the candlelit room, it was hardly noticeable.

“How about you make yourself comfortable on the couch?” he proposed, “I’ll just take a moment to clear up the dishes and join you.”

You agreed, unfazed by his abrupt suggestion, making your way to the couch. It suddenly struck you how quiet it was, so you set your glass of wine on the coffee table and sat on your side on the floor by the cassette deck to choose some after dinner music. Shuffling through the collection of tapes, you found the perfect one and began to play it. The memorable strumming of the classic [rock song](http://t.umblr.com/redirect?z=https%3A%2F%2Fyoutu.be%2FTj75Arhq5ho&t=MjM0MTFiNGIyNDU0YmU0ZTFhOWI1MGQzM2E1ZmJlMjBkMjNlODUyYSxFS2YzdXh3dw%3D%3D&b=t%3AZx5fO4IhIhjEdxyW5irvTA&m=1) began and you sensed Sam standing behind you.

Turning around, you looked up to see a bemused expression on his face.

“Metallica? Really?”

“You don’t approve?” you challenged with a smirk.

“I most certainly do approve,” he politely reached out a hand in front of you to help you up from the floor. Once you slipped your hand in his, he helped you up, pulling you towards him, as his other hand rested on the small of your back to hold you close. The grasp on your hand loosened as Sam angled his hand until your palms were touching.

“May I have this dance?” he murmured, his eyes staring into yours as he slowly began to sway.

The playful mood suddenly felt intimate. Ever since you agreed to take it slow with him, you’ve respectfully kept your distance, as did he. The two of you didn’t even hold hands since that first date, so to have him pull you into this embrace, feeling the warmth of his body, and knowing that he wanted to be close to you made your heart begin to race.

You swayed along with Sam, not saying anything. The two of you searched each other’s eyes, listening to lyrics:

_Never opened myself this way_  
Life is ours, we live it our way  
All these words I don’t just say  
And nothing else matters

The swaying stopped as Sam gently flitted his eyes to your mouth. You began feeling flustered then, quickly swiping your tongue over your lips in a nervous gesture.

At the action, his eyes immediately met yours with a teasing glint

“Didn’t you bring over some chocolates?”

You chuckled breathily at the random question, “Uh, yeah.”

“Have a seat,” Sam instructed, stepping away from you.

The sudden loss of his embrace made you shiver for a second, feeling light-headed.

Sam rushed back to sit beside you, opening the small gold box to reveal a small, decadent selection of dark chocolate truffles. Each one looked slightly different but all looked sinfully delicious.

“Which one looks good to you?” he offered the box to you.

You pointed to the truffle dusted in a red cocoa, “This one. It’s new, it’s supposed to be a little spicy.”

“Spicy?” Sam’s eyebrows raised examining the truffle, his own tongue swiped his lips before exchanging a sensuous gaze at you.

Delicately, he picked up the truffle while speaking, “I want to try something,” he guided the truffle to your mouth, “hold this between your lips.”

You parted your lips, ever so gently biting down on the truffle to hold it in your mouth. The powdery exterior of the truffle was mildly sweet, but you couldn’t taste much more than that.

Sam’s eyes darkened with lust when he saw you focus on him, waiting with your lips wrapped around the chocolate. He leaned in, his own lips now parting, fitting and brushing against yours as his surrounded the chocolate. It was a sensual tease that you desperately wanted to end so much you could taste it, literally. The truffle began to melt from the heat of both of your lips.

But chocolate wasn’t the only thing melting.

A whimper escaped your lips leading Sam to end the tease and expertly bit down, the bite of chocolate immediately melted away in your mouths.

It was an oral adventure as the both of you savored the deep, dark flavor of cocoa against your tongues until the chocolate was no more. But then, you felt it, the hint of spice began to simmer in the back of your throat and you hummed into the kiss. Sam delve his tongue to explore your mouth, tasting your sweetness, making you shudder.

The feeling of your arousal getting wetter made you moan. Once he heard the sounds you were making, Sam’s hands wrapped around you, pulling you onto his lap. He let out a groan and your eyes opened wide once you felt why.

You pushed against his chest, pulling back from the kiss with a little more force than you intended. A look of bewilderment appeared on your face as you looked at nothing. You were shocked at the feeling of his hard length against your sweater dress covered ass, the flimsy material not hiding how swollen he was or how warm you felt.

“You ok?” he asked concerned as his hand cupped your face. His thumb gently brushed your swollen lip, calming you until your eyes fluttered shut.

“I-I’m good,” you replied, eyes still closed so you could concentrate. “I just thought, you wanted to take things slow?”

“Y/N, open your eyes,” he whispered.

Slowly, you opened your eyes to see a hunger in his.

“I’ve missed you so much. I don’t want to wait any longer, I don’t want to take things slow anymore. I just want you.”

It was everything you wanted to hear in that moment.

“I want you too,” you purred, quickly crashing your lips back to his. Your hips had a mind of their own, grinding into his lap.

Sam grunted as he pulled away from the kiss. With a look of determination and nostril flaring, he stood up, lifting you in his arms and began walking towards his bedroom. It was like something out of a romance novel, the prince finally carrying the princess off to bed her in a hot and steamy page turner.

You couldn’t wait to finally be together with Sam.

_I’m walking on sunshine, whoa…_

Nope! Of course, your trusty ringtone had to make an appearance at this moment. Sam halted, being the gentleman that he is and looked to you with desperation.

“Ignore it,” you demanded with no hesitation.

Without a beat, Sam continued to walk to his bedroom.

_It’s the eye of the tiger,_  
It’s the thrill of the fight  
Rising up to the challenge of our rival…

Sam stopped once again, his mouth tense.

“Dean,” he explained his ringtone in annoyance before shaking his head and proceeded to his bedroom, “Ignoring it!”

When Sam finally entered the room he tossed you onto the king size bed, making you yelp in delight. You raised yourself up on your elbows to see him crawl up your body until his face was inches away from yours. Not wanting to wait any longer, you pulled him towards you as your lips met once again. It felt amazing having his body surround you, close just like you wanted him but his swollen bulge was making you needy.

Sam must have been just as needy as his large hands roamed down your clothed body. You gasped into the kiss when you felt his fingertips finally met your bare skin at your thighs, just at the hem of your sweater dress. He took the opportunity of your gasp to drift his lips to your neck, making you heady with lust as you panted. His hands dipped underneath the skirt, willowy fingers sliding onto your hips.

_*tap tap tap*_

You both froze for a minute looking at each other with confused expressions, uncertain if you were hearing noises or was it real.

A few seconds passed before a smirk appeared on Sam’s face as he proceeded to hook his fingers onto the waistband of your panties….

_*KNOCK KNOCK KNOCK*_

“Sam! Sammy!” a muffled voice called out along with loud banging on the door, much to the frustration of both you and Sam.

With an exasperated groan, you lay your head back on the bed as Sam remained quiet as his hands left your body.

“I will be right back,” Sam enunciated each word with a sexy conviction that made you crash your lips against his, kissing him briefly and full of desperation.

He forced himself to pull away, standing up, smoothing out his hair and adjusted himself.

“Fuck me,” he angrily muttered to himself a little too loud when he turned to leave the bedroom.

“Oh, I want to so bad,” you whispered to no one, clenching your thighs together.

While you lay frustrated on the bed, you overheard Sam already scolding his visitor while he opened the door.

“What the fuck is it, Dean? I’m busy!”

The calm, husky voice of the older Winchester replied, “We’ve got to leave now. Cas needs us.”


	7. Damn it, Kevin!

**Summary for the Chapter:**

> The interruption of your romantic evening with Sam turns out to be more of a hassle leading you to a tireless night.

**Notes for the Chapter:**

> Text exchanges are bolded and italicized. It’s been a while but Model!Sam is back! Planned for a longer fic but I got impatient. Feel free to send me any feedback. I’d love to hear from you!

([x](http://exbloodjunkie.tumblr.com/post/44666722535))

“Cas needs us.”

Overhearing the serious tone of the older Winchester echo through your head, you instantly felt the adrenaline spike through your body.  The anxious concern destroyed any arousal you had moments prior. Dean’s phone call, followed by the fact that he was immediately at Sam’s doorstep dictated that this was an emergency.

Everything happened so fast that you didn’t question a thing as you walked out of Sam’s room with a look of concern. You didn’t ask why Dean grabbed Sam’s arm without explanation and dragged him to his room. You didn’t ask why Kevin was also there, taking your hand and tugging you outside. You didn’t ask if you could say a few seconds to say goodnight to Sam, only the rushed split second of somber yet hopeful glances at each other had to suffice.

As Kevin steered you out the door and onto the street, he kept apologizing for the interruption. You focused on following him through the darkness, keeping up as he hurried through the patches of midnight black that scattered through the soft orange hues of the street lights. Seconds later he led you to a familiar looking van before he began to explain the situation. You listened intently still feeling that pit of worry in your stomach that froze after you heard the words _photo shoot_.

Your romantic evening with Sam was cut short due to a photo shoot?

It wasn’t until you took your seat on the passenger side of the van that it finally dawned on you that this was the _Crossroads_  van to transport clothes and accessories for remote photo shoots and this was not a real emergency.

This was utter bullshit. The fight or flight response in your body was immediately replaced by anger and by the time Kevin settled into the driver’s seat, you were absolutely livid.

Resentfully, you folded your arms across your chest and mocked Dean’s gruff voice, “Cas needs us.”

“What’s that for?” Kevin chuckled at your exaggerated imitation as he put the keys into the ignition, while your icy cold stare shot daggers at him.

“You _know_ what! Really, Kevin? A photo shoot? I-I don’t even wanna talk to you right now,” you snapped, making him shrink in his seat as he started the van and remained silent.

In that moment, you didn’t feel guilty for being curt with your friend. After all, it was both Dean _and_  Kevin who showed up at Sam’s door and rudely interrupted your, um,  _after dinner activities_. They both knew it was the first time that you’ve seen each other in ages. Both were witnesses to your sickening sweet messages to each other on your phones. The least they could’ve done was be upfront with you, but Dean’s serious tone made it seem as if Cas was in dire need of help.

* * *

You stewed in your frustrations as you continued your silent treatment as Kevin drove to an unknown destination. He was cautious, a glint of fear in his eyes as he looked at you every couple seconds and then to the dashboard as if he were wary that you’d claw his eyes out if he were to turn on the radio to fill in the angered silence. The drive felt long and unsettled. The quiet was almost deafening, bordering on awkward as you recognized how uncomfortable your friend looked. You knew Kevin didn’t want to be put in this place, to begin with, he was just doing his job.

Sympathy finally took over as you uncrossed your arms and huffed out as if the sharp exhale would help to dissolve your agitations. At that Kevin’s eyebrows perked up, his eyes wide and hopeful as he glanced over to gauge your mood.

Resigning yourself from the silence, you muttered, “Ok, fine. Tell me what’s the big deal with this photo shoot and it better be good.”

Kevin nodded before spouting off the explanation as if he memorized it from a script, “It’s a secret photo shoot that was planned in a rush. Castiel has been tinkering with designing women’s formal wear…”

You nodded in acknowledgment, your mind already wandering away, flooding with the thought that you were the inspiration. Did your design of Charlie’s dress make an impression on Castiel that evening of his fashion show? Or was he already designing it? You hoped it was you who managed to influence one of your favorite designers.

When the van came to a stop, you noticed that you arrived at the office and that Kevin was still talking as he exited the van. Promptly you got out to follow him.

“…that’s where _Crossroads_ comes in, we’re supposed to have the exclusive scoop but we’ve got a deadline, as always.”

“Ok, hold up,” you put your hand up in the air in a halting motion, “I have so many questions right now but my first is why the hell didn’t you even give me a clue that any of this was happening? I mean-”

He interrupted defensively, “Hey, I was just doing my job. You know how it is, Y/N, only a handful of people were supposed to know.”

You stopped in your tracks, “Who else knew?”

Kevin casually shook his head while he listed the names, “Well, me… Castiel… Crowley… Jodyyyy,” he trailed quietly, eyes shifting away from you before murmuring the last name, “and Charlie.”

Your eyes bulged out in shock, “Oh come on! _Charlie_ knew?!”

He motioned his hands impatiently, “You can yell at me later but we gotta move. We’re already behind schedule enough as it is.”

As you followed Kevin into the fashion closet, it finally dawned on you that all those swatches Jody recently gave you were for this secret photo shoot. You began to panic, rethinking, and questioning every single item as Kevin attempted to pack everything into the van. It was a mad scramble as you picked up additional accessories now knowing the context of the photo shoot, much to Kevin’s chagrin.

It took longer than anticipated to get everything to fit in the van, but it all came together. You were exhausted as Kevin drove you home, longing to get to bed for a good night’s sleep, and a chance to contact Sam. When you dragged yourself out of the van with a yawn, you missed Kevin muttering something about giving you an hour.

“Sorry? I didn’t catch that. An hour for what?”

“To pack. You’re coming along to this photo shoot too,” he explained.

You threw your hands in the air, exclaiming, “Damn it, Kevin! We need to work on your communication skills!”

* * *

You never once thought that a road trip accompanied by Kevin and Charlie, your two best friends, would be burdensome. But this wasn’t like any other road trip you’ve been on. For one, you had no idea where you were going. You didn’t know how long the trip would be and for how long you were going for. Who knew those details anyway? Oh right, your friends did. It’s not like you couldn’t have asked but your frazzled mind was so focused on packing the essentials that it didn’t occur to you to ask the simple question.

Your fondness for Charlie and Kevin was questionable at this point in the wee hours of the night as they were awake, alert, and already prepared for the long trip ahead unlike you, who had a hastily packed a bag in under an hour. Kevin was smart enough to sneak in a nap while you packed and was now sipping on an extra large coffee to keep him attentive for the drive. Charlie was sitting shotgun, already well rested in advance as she clicked away at her laptop, getting a head start on her notes for coverage on the photo shoot. You sat behind them, utterly exhausted, but worry kept your mind buzzing about as you mentally listed what you packed, trying to remember if you forgot anything important.

Realizing you still didn’t know your final destination, you asked the question, involuntarily sounding slightly whiny, “I still have no clue where we’re going. Are we almost there?”

You sensed both of them rolling their eyes at your clichéd question.

“No, we’re here now,” Kevin replied with dry sarcasm.

Charlie, wanting to get in on the fun, chirped in, "Don’t worry Y/N, we’ll get there when we get there.”

You shook your head muttering at them, “I hate you two… so much… you don’t even know.”

They replied with mocked sympathy in a synchronized ‘awwww’.

“Seriously, though, just get some sleep, Y/N. We’ve got a full schedule ahead,” Kevin affirmed.

You wished you could sleep, but you were so unnerved from not having a moment of peace since you left Sam’s place.

Sam.

He must’ve been just as frustrated as you when he found out about the photo shoot. The thought of him giving Dean a hard time like you did with Kevin made you smile. It’s been such a harried, emotional rollercoaster that you realized that you didn’t get a chance to check your phone. Upon seeing a notification of several missed texts, your spirits were lifted as you began to read them.

**Can’t believe I need to go to yet another photo shoot. :(**

**I would hate it if you believed that the universe is trying to tell you something since our timing hasn’t been the greatest.**

**If anything, all these interruptions are making me want you more than ever.**

**BTW did I tell you how sexy you looked tonight? ;)**

**I’m so upset I didn’t even get a chance to give you a proper good night kiss.**

**IOU a good night kiss xxx**

**Damn it, was hoping you’d reply by now. Anyway, I’ll call or text you if I get a chance tomorrow morning. Sleep well, beautiful.**

**Sorry, just one more text to let you know I can’t get you out of my head <3**

Your heart fluttered, reading and re-reading each text. Instantly, you began texting Sam knowing he’d read them in the morning.

_I’m smiling so much right now reading all your texts. You’re so amazing xox_

_I think I just need to accept that surprise photo shoots are a thing in this line of work and not take it out on people. I gave Kevin a bit of the ‘ol silent treatment after I found out. Oops!_

_Don’t worry, the only thing the universe is telling me is that good things come to those who wait. ;)_

_I want you too, Sam. I’ve been wanting more for a while, actually…_

_I know we didn’t get a chance to say good night but I have a feeling I’ll be seeing you soon enough._

_BTW, is that IOU only good for kisses at night? Can it be redeemed in the morning?_

You hoped that it would be a surprise for Sam to see you at the photo shoot. At least you could take comfort in the fact that this would be the first photo shoot you’d be at together.

With contentment, you put your phone away and settled into a comfortable position. Finally closing your eyes you began thinking about how warm and safe you felt in Sam’s strong arms when you swayed to the music earlier in the evening. Thoughts of Sam and knowing that you’d see him again soon calmed your nerves as you drifted to sleep.


End file.
